Online Dating: Advice From Grace Lee, An NYC Dating Coach

As women over 50, we’ve seen the dating world go through a lot of changes—and now, so much of dating is done online. There are numerous websites, apps, and services you can use to meet people, all of which expand our dating pool and, in theory, increase our chances of finding love and companionship. But even with these upsides in mind, online dating can feel like a big question mark to many people. It can feel intimidating, daunting, hopeless, or scary, depending on your situation and dating history. Also, until you’ve been on the apps and sites, there are a lot of unknowns in the equation. Here to demystify a bit of the online dating world is New York-based dating coach Grace Lee! Read on to see my interview with her, which includes practical tips for dating online, from your mindset to profile photos. 

Grace, I’m so glad to be interviewing you for the blog! For readers who aren’t familiar with you and your work, can you give us a little background about yourself? 

Of course! As you know, I’m a dating coach based in NYC, and I work with clients ranging from their 20s to their 80s, in locations all over the country. I help them set up their profiles and I even work with clients one on one on their dating skills through virtual reality dating. 

I’ve been in the dating industry for years in three ways. The first, and the most common, is that I was single. I was married for 10 years and then got divorced. I’m a single parent, and now I’m in a relationship, but I was dating for about 10 years, so I have extensive experience in all of the apps and have been on many, many, many dates. So I’ve been a user and a dater, but for a time, I also worked as a matchmaker. I went around the city, met with hundreds of men and women of all different ages, and all different occupations. What I saw was that all of these people had hit a wall with dating—so much so that they were willing to pay an external party to help find a match. I found that the part I was most interested in was really why it wasn’t working out rather than helping them find a specific person. After a short stint doing that, I realized I wanted to focus on helping people and in particular, helping people with the technology of dating, because I felt really comfortable and confident with those. I started my own date coaching business, called A Good First Date. I focus on helping people figure out their brand—who they are, and who they want to attract—and other issues they face while they’re on dates or when they’re messaging/texting. 

So you work with clients on the nitty gritty? Building their Hinge or Match.com profiles? 

I do—it’s harder than most people expect. It forces you to be really concise! You get 300 characters, six photos, and a bunch of checkboxes to tell other people who you are, what makes you special, and what you want. And we have to communicate that in an accessible way. It’s a tall order. I also do date coaching in virtual reality—so people show up as avatars and I lead them through different exercises in things that would come up on dates. For instance, on a date someone will probably ask the other person where they’re from. So I coach my client and help them determine how they’re going to interact, what their body language will look like, all of that stuff. Virtual reality is a huge game changer for date coaching, because I’m really able to understand what’s happening in the moment and help people with their soft skills in a way that no one has been able to before. 

Very cool. Okay, so let’s dive in. First off, why do you think many people, especially women over 50, are nervous to start online dating?

I think in general there’s a hesitation to jump into online dating because it’s new to them. I think it’s becoming less of an issue, but users in that bracket are sticking with the older sites like Match.com, and they’re not really as active on the newer sites. Part of being successful with online dating is, you know, where are the most people? There aren’t as many people in that age range on these newer platforms, as a result, those groups are underserved on the newer platforms. Also, there are some other factors. First, there’s a concern that they don’t know what they’re doing. There are also concerns about safety, and I think for people who haven’t been online before, that can get blown out of proportion a bit. There are a lot of ways to minimize the danger or harassment you might read about. Those feelings are valid, but I think it’s important for people of all ages to be using these platforms. 

I think so too, but I definitely also see the concerns. Do you think part of it has to do with insecurity? Or bad dating experiences? 

Yes for sure. I think our culture kind of celebrates these bad dating stories—we all know at least one person who has a bad dating story, or maybe we’ve been that person. We want to hear about bad dating stories and people want to talk about what a jerk this person was or how disappointing it was. Honestly, I think it creates a whiny, loser culture around dating, and when you buy into that side of dating, you’re going to feel negatively about it. You’re going to think that no one is good enough and it’s a waste of your time, and you’re going to show up on the dating apps jaded! You’re going to communicate in a way that’s cagey and suspicious, and when you show up on the date, you’re like, interviewing the person. I think one of the biggest challenges I face as a coach is getting people in the right mindset—a mindset that will help them be successful. 

As for insecurity, that’s definitely part of it too. With online dating, it’s a completely different scale of all the emotions you would feel from dating in a pre-online world. Let’s take rejection for instance. Before online dating, you might have gotten rejected every few months; on a dating app, you could be rejected 100 times in three minutes. We are vulnerable to a lot of judgment. So we need new tools around how to interpret that and how to toughen up so we aren’t thrown off by all these things and we can still have fun with dating. 

That’s all very true. So, how do we represent ourselves better online? What are some of your tips?

So let’s start with pictures, because there’s a lot of room for error. Your pictures should all come together to address three questions: 1) Who are you? 2) What makes you interesting? 3) How can I start a conversation? 

First is “who are you”—this really gets at your interests and what makes you you. Are you active? What are your hobbies? What do you like to do, and how can you show that? For me, I love music, and I can talk to pretty much anyone about music, so I might put a photo of me at a concert or music festival, because it could start a conversation with someone who also loves music.

What makes you interesting—by this, I mean what makes you interesting to yourself. Like why would you choose yourself? What are the things about yourself that you think are interesting? (Not what you think other people would find interesting—we’re trying to find good matches, not just more matches.) 

And third, starting a conversation. You want to start a conversation that’s meaningful. So try to think about a topic of conversation that you feel really excited to talk about and that you’re comfortable talking about. That way, when someone asks you about it, you’re already excited to have that conversation and you aren’t trying to find something to say, because you already have a lot to say. Again, for me, that’s music. You want to set yourself up for success by choosing a topic that interests you, and displaying that through your photos. If you love hiking and could talk about hiking for days, you could put a picture of you hiking in your favorite place.

It really comes down to being in touch with who you are, what you’re looking for, and what conversations you want to have with other people. That’s why I think people really benefit from having another person help them through the process of putting a profile together, because it’s hard! We’re so rarely asked to put together something like that. 

I love those tips. What about advice for women who have seen the landscape change a lot since they were last dating? For instance, if you are divorced (newly or not) or windowed, it’s probably been a while since you’ve last had to date, and a lot has changed in that time. 

I think a lot of women in that demographic have dated to find a husband, or a long-term relationship, in a way that’s different than younger people. And many women who were married to someone and had a really great relationship, and that person was the love of their life, when they get back out there and start dating again, no one is measuring up to that person they were with. Or, a bit different, no one is marching up to the person they think that they should be with (there’s a nuance there). To those women, I would say that mindset is especially important. This isn’t one of those things where you’re going to just get in and get out. You’re not going to get this shit down and get back out. You really have to approach it with a sense of curiosity and adventure, and just be able to have fun with it. 

Like if you show up to a date, and you don’t find the other person attractive…so what? It doesn’t make you unattractive. I think we have to approach dates like, “Oh, this could be a cool person. Let’s see what happens.” Go into it with the mindset of “I’m going to make the most of it and see what happens.” With that attitude, you end up putting less pressure on yourself, on the date, and you stay open-minded. The game isn’t “Oh I want to find out what’s wrong,” it’s “I want to find out what’s right.” I want to have a fun conversation. I want to get to know this person. Maybe one thing leads to another and you end up doing something really fun or they end up being a significant person in your life, and maybe it was just a good first date. That’s okay!

I really love that advice. I’m all about shifting our mindsets—whether that’s with fitness, nutrition, aging, or in this case, dating. Thank you so much for all of your expertise! Any final words of advice or encouragement for anyone out there who’s starting to date or currently dating?

Dating can be like a numbers game—it’s like a lottery. The more tickets you buy, the more chances you have. But you also need to know what’s a winning ticket. Let’s take a step back and think about what we’re doing here. We’re trying to find someone who really fits. It’s like a puzzle. You want to have a unique shape that matches with another unique shape, but unless you know what your shape is, it’s hard for you to match with other shapes. You don’t need 1000 matches—you want fewer, better matches. Try to take the pressure off of dating and just take it for what it is: a night out with someone new. It’s nice to be taken out for a drink once in a while. It’s fun to dress up and have a nice conversation. Let your goal be to make the most of it, stay open-minded, and have fun with it. 

If you enjoyed this interview with Grace, I encourage you to join our membership-only community, the Pure Joy Squad! 

Xo, 

Renata